So my friend and I are switching PS3s and I have a bunch of Playstation Plus items I've downloaded for free, and I'd like to know if anyone has any experience transferring items you've downloaded with PS Plus to a new console. Should I be using the Transfer Utility like usual or is there an easier way.

What do you mean your switching PS3s? If you are transferring to a new PS3 the transfer utility should get all your stuff including your Plus content. I transferred from a 40GB to a 160GB a year ago and everything transferred no problem.

You could just activate your PSN account on the new PS3 and redownload everything from your download list. But if you've got lots content that can be a bit cumbersome, so using the transfer utility will probably provide a smoother experience.

Transfarring

I may try the download history to try and download everything over night.

That should work. Just log in to your PSN account on the new PS3. However, you will want to deactivate that same account on your old PS3 if you aren't going to be using it I think.

I had an issue with one of my accounts where I couldn't rent a movie because it was being used on too many PS3s. I deactivated it on one of them but it never fixed the problem. Just made a new account because there wasn't much content on the other one anyway.